CA2818018C - Liposomal formulation of dalcetrapib - Google Patents
Liposomal formulation of dalcetrapib Download PDFInfo
- Publication number
- CA2818018C CA2818018C CA2818018A CA2818018A CA2818018C CA 2818018 C CA2818018 C CA 2818018C CA 2818018 A CA2818018 A CA 2818018A CA 2818018 A CA2818018 A CA 2818018A CA 2818018 C CA2818018 C CA 2818018C
- Authority
- CA
- Canada
- Prior art keywords
- composition according
- methylpropanethioate
- amino
- phenyl
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 83
- YZQLWPMZQVHJED-UHFFFAOYSA-N 2-methylpropanethioic acid S-[2-[[[1-(2-ethylbutyl)cyclohexyl]-oxomethyl]amino]phenyl] ester Chemical compound C=1C=CC=C(SC(=O)C(C)C)C=1NC(=O)C1(CC(CC)CC)CCCCC1 YZQLWPMZQVHJED-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 229950004181 dalcetrapib Drugs 0.000 title description 16
- 238000009472 formulation Methods 0.000 title description 9
- 239000002502 liposome Substances 0.000 claims description 50
- 239000000787 lecithin Substances 0.000 claims description 27
- 235000010445 lecithin Nutrition 0.000 claims description 24
- 150000003904 phospholipids Chemical class 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000003381 stabilizer Substances 0.000 claims description 18
- 229940067606 lecithin Drugs 0.000 claims description 17
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 15
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 13
- 235000010355 mannitol Nutrition 0.000 claims description 11
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 10
- 239000012528 membrane Substances 0.000 claims description 10
- 229930195725 Mannitol Natural products 0.000 claims description 9
- 239000008344 egg yolk phospholipid Substances 0.000 claims description 9
- 239000000594 mannitol Substances 0.000 claims description 9
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 8
- 229930006000 Sucrose Natural products 0.000 claims description 7
- 239000005720 sucrose Substances 0.000 claims description 7
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 6
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 6
- 150000001720 carbohydrates Chemical group 0.000 claims description 6
- 235000014633 carbohydrates Nutrition 0.000 claims description 6
- 239000000600 sorbitol Substances 0.000 claims description 6
- 235000010356 sorbitol Nutrition 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 5
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 5
- 235000012000 cholesterol Nutrition 0.000 claims description 5
- 235000013601 eggs Nutrition 0.000 claims description 4
- CITHEXJVPOWHKC-UUWRZZSWSA-N 1,2-di-O-myristoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC CITHEXJVPOWHKC-UUWRZZSWSA-N 0.000 claims description 2
- KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 claims description 2
- SNKAWJBJQDLSFF-NVKMUCNASA-N 1,2-dioleoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/CCCCCCCC SNKAWJBJQDLSFF-NVKMUCNASA-N 0.000 claims description 2
- KILNVBDSWZSGLL-UHFFFAOYSA-O 2-[2,3-di(hexadecanoyloxy)propoxy-hydroxyphosphoryl]oxyethyl-trimethylazanium Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-UHFFFAOYSA-O 0.000 claims description 2
- 239000005715 Fructose Substances 0.000 claims description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 claims description 2
- 229930091371 Fructose Natural products 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 claims description 2
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 2
- 229960003724 dimyristoylphosphatidylcholine Drugs 0.000 claims description 2
- 150000002016 disaccharides Chemical class 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 2
- 150000002772 monosaccharides Chemical group 0.000 claims description 2
- 150000008104 phosphatidylethanolamines Chemical class 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 125000000185 sucrose group Chemical group 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 239000000811 xylitol Substances 0.000 claims description 2
- 235000010447 xylitol Nutrition 0.000 claims description 2
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 2
- 229960002675 xylitol Drugs 0.000 claims description 2
- 235000010469 Glycine max Nutrition 0.000 claims 1
- 244000068988 Glycine max Species 0.000 claims 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 14
- 238000002360 preparation method Methods 0.000 abstract description 6
- 238000011282 treatment Methods 0.000 abstract description 4
- 201000010099 disease Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 56
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 31
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- 239000003814 drug Substances 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 239000008194 pharmaceutical composition Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 208000024172 Cardiovascular disease Diseases 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 241000124008 Mammalia Species 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 6
- 201000001320 Atherosclerosis Diseases 0.000 description 5
- 208000000563 Hyperlipoproteinemia Type II Diseases 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 201000001386 familial hypercholesterolemia Diseases 0.000 description 5
- 150000002632 lipids Chemical class 0.000 description 5
- 238000003760 magnetic stirring Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 235000013772 propylene glycol Nutrition 0.000 description 5
- 229960004063 propylene glycol Drugs 0.000 description 5
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 4
- FFAADXOKPZHULO-UHFFFAOYSA-N 2-methylpropanethioic s-acid Chemical compound CC(C)C(S)=O FFAADXOKPZHULO-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 208000029078 coronary artery disease Diseases 0.000 description 4
- 229940083466 soybean lecithin Drugs 0.000 description 4
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 3
- 206010002383 Angina Pectoris Diseases 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 208000035150 Hypercholesterolemia Diseases 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- 206010021024 Hypolipidaemia Diseases 0.000 description 3
- 241000282567 Macaca fascicularis Species 0.000 description 3
- 208000018262 Peripheral vascular disease Diseases 0.000 description 3
- 239000004148 curcumin Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- -1 glycolfurol Chemical compound 0.000 description 3
- 208000006575 hypertriglyceridemia Diseases 0.000 description 3
- 208000029498 hypoalphalipoproteinemia Diseases 0.000 description 3
- 208000028867 ischemia Diseases 0.000 description 3
- 208000010125 myocardial infarction Diseases 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 239000007916 tablet composition Substances 0.000 description 3
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 description 2
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- 208000032928 Dyslipidaemia Diseases 0.000 description 2
- 208000037487 Endotoxemia Diseases 0.000 description 2
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 2
- 208000017170 Lipid metabolism disease Diseases 0.000 description 2
- 102100024640 Low-density lipoprotein receptor Human genes 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 2
- 206010063837 Reperfusion injury Diseases 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- 206010045261 Type IIa hyperlipidaemia Diseases 0.000 description 2
- ATBOMIWRCZXYSZ-XZBBILGWSA-N [1-[2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] (9e,12e)-octadeca-9,12-dienoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C\C\C=C\CCCCC ATBOMIWRCZXYSZ-XZBBILGWSA-N 0.000 description 2
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000003304 gavage Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 208000031225 myocardial ischemia Diseases 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 235000020824 obesity Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 208000037803 restenosis Diseases 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- KEWSCDNULKOKTG-UHFFFAOYSA-N 4-cyano-4-ethylsulfanylcarbothioylsulfanylpentanoic acid Chemical compound CCSC(=S)SC(C)(C#N)CCC(O)=O KEWSCDNULKOKTG-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 102100037637 Cholesteryl ester transfer protein Human genes 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- CZMRCDWAGMRECN-FBXJDJJESA-N D-sucrose Chemical compound O[C@@H]1[C@@H](O)[C@H](CO)O[C@]1(CO)O[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](CO)O1 CZMRCDWAGMRECN-FBXJDJJESA-N 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 101000880514 Homo sapiens Cholesteryl ester transfer protein Proteins 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 238000008214 LDL Cholesterol Methods 0.000 description 1
- 239000000232 Lipid Bilayer Substances 0.000 description 1
- 240000008790 Musa x paradisiaca Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002296 dynamic light scattering Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 238000001294 liquid chromatography-tandem mass spectrometry Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/265—Esters, e.g. nitroglycerine, selenocyanates of carbonic, thiocarbonic, or thiocarboxylic acids, e.g. thioacetic acid, xanthogenic acid, trithiocarbonic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
- A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Emergency Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Dispersion Chemistry (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10194219 | 2010-12-08 | ||
| EP10194219.1 | 2010-12-08 | ||
| PCT/EP2011/071698 WO2012076443A1 (en) | 2010-12-08 | 2011-12-05 | Liposomal formulation of dalcetrapib |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2818018A1 CA2818018A1 (en) | 2012-06-14 |
| CA2818018C true CA2818018C (en) | 2016-02-02 |
Family
ID=43875204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2818018A Expired - Fee Related CA2818018C (en) | 2010-12-08 | 2011-12-05 | Liposomal formulation of dalcetrapib |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20120148662A1 (ja) |
| EP (1) | EP2648698A1 (ja) |
| JP (1) | JP5729735B2 (ja) |
| KR (1) | KR101546171B1 (ja) |
| CN (1) | CN103237542A (ja) |
| BR (1) | BR112013014291A2 (ja) |
| CA (1) | CA2818018C (ja) |
| MX (1) | MX2013006031A (ja) |
| RU (1) | RU2013129777A (ja) |
| WO (1) | WO2012076443A1 (ja) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140335166A1 (en) * | 2013-05-08 | 2014-11-13 | Michael W. Fountain | Methods of Making and Using Nano Scale Particles |
| CN111073974B (zh) | 2013-03-27 | 2024-04-09 | 豪夫迈·罗氏有限公司 | 用于预测对于治疗的响应性的遗传标记 |
| US9599417B2 (en) | 2014-05-15 | 2017-03-21 | Savage Arms, Inc. | Extractor mechanism for firearm |
| CA2953483C (en) * | 2014-07-30 | 2023-04-04 | F. Hoffmann-La Roche Ag | Genetic markers for predicting responsiveness to therapy with hdl-raising or hdl mimicking agent |
| SG11201903326RA (en) * | 2016-10-28 | 2019-05-30 | Servier Lab | Liposomal formulation for use in the treatment of cancer |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6447800B2 (en) * | 1996-01-18 | 2002-09-10 | The University Of British Columbia | Method of loading preformed liposomes using ethanol |
| JP2894445B2 (ja) | 1997-02-12 | 1999-05-24 | 日本たばこ産業株式会社 | Ｃｅｔｐ活性阻害剤として有効な化合物 |
| WO2001056579A1 (en) * | 2000-02-04 | 2001-08-09 | Esperion Therapeutics Inc. | Methods for treating alzheimer's disease |
| JP2004524368A (ja) * | 2001-03-27 | 2004-08-12 | フェアーズ ファーマシューティカル リサーチ エヌ．ヴェー． | 低い水溶性を有する生物学的に活性な化合物を可溶化するための方法および組成物 |
| JP2003119120A (ja) * | 2001-10-12 | 2003-04-23 | Masahiko Abe | リポソームの製造方法、及び該リポソームを含有する化粧料、及び皮膚外用剤 |
| DK1603553T3 (da) * | 2003-03-17 | 2012-01-30 | Japan Tobacco Inc | Farmaceutiske præparater af CETP-inhibitorer |
| WO2005117869A1 (en) * | 2004-05-12 | 2005-12-15 | Sepracor Inc. | Combinations comprising (s)-amlodipine and a cholesteryl ester transfer protein inhibitor, and methods for reducing hypertension |
| WO2006004903A2 (en) * | 2004-06-28 | 2006-01-12 | Atherogenics, Inc. | 1,2-bis-(substituted-phenyl)-2-propen-1-ones and pharmaceutical compositions thereof |
| AU2005272946B2 (en) * | 2004-08-10 | 2012-01-12 | Talon Therapeutics, Inc. | Compositions and methods for treating leukemia |
| EP1896074A4 (en) * | 2005-05-25 | 2009-04-22 | Liponex Inc | PHARMACEUTICAL COMPOSITIONS FOR THE TREATMENT OR PREVENTION OF CORONARY ARTERY DISEASE |
| US7435849B2 (en) | 2005-10-31 | 2008-10-14 | Hoffmann-La Roche Inc. | Process for the production of acid chlorides |
| EP1935867A1 (en) | 2006-12-20 | 2008-06-25 | F. Hoffmann-La Roche Ag | Process for preparing 1-(2-ethyl-butyl)-cyclohexanecarboxylic acid |
| SG172003A1 (en) * | 2008-12-08 | 2011-07-28 | Hoffmann La Roche | Combined drug administration |
| RU2489145C1 (ru) * | 2009-04-29 | 2013-08-10 | АМАРИН КОРПОРЕЙШН ПиЭлСи | Фармацевтические композиции, содержащие ера и сердечно-сосудистое средство, и способ их применения |
-
2011
- 2011-12-05 JP JP2013542485A patent/JP5729735B2/ja not_active Expired - Fee Related
- 2011-12-05 RU RU2013129777/15A patent/RU2013129777A/ru unknown
- 2011-12-05 KR KR1020137017611A patent/KR101546171B1/ko not_active IP Right Cessation
- 2011-12-05 WO PCT/EP2011/071698 patent/WO2012076443A1/en active Application Filing
- 2011-12-05 BR BR112013014291A patent/BR112013014291A2/pt not_active IP Right Cessation
- 2011-12-05 MX MX2013006031A patent/MX2013006031A/es unknown
- 2011-12-05 CA CA2818018A patent/CA2818018C/en not_active Expired - Fee Related
- 2011-12-05 CN CN2011800585700A patent/CN103237542A/zh active Pending
- 2011-12-05 EP EP11807875.7A patent/EP2648698A1/en not_active Withdrawn
- 2011-12-06 US US13/311,640 patent/US20120148662A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN103237542A (zh) | 2013-08-07 |
| US20120148662A1 (en) | 2012-06-14 |
| KR101546171B1 (ko) | 2015-08-20 |
| KR20130113494A (ko) | 2013-10-15 |
| CA2818018A1 (en) | 2012-06-14 |
| JP2013544861A (ja) | 2013-12-19 |
| WO2012076443A1 (en) | 2012-06-14 |
| MX2013006031A (es) | 2013-07-15 |
| JP5729735B2 (ja) | 2015-06-03 |
| BR112013014291A2 (pt) | 2016-09-20 |
| EP2648698A1 (en) | 2013-10-16 |
| RU2013129777A (ru) | 2015-01-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2632433C2 (ru) | Липидный преконцентрат с замедленным высвобождением фармакологически активного вещества и фармацевтическая композиция, содержащая его | |
| US5665379A (en) | Lipid particle forming matrix, preparation and use thereof | |
| US10028911B2 (en) | Sustained release formulation of methotrexate as a disease-modifying antirheumatic drug (DMARD) and an anti-cancer agent | |
| RU2216315C2 (ru) | Способ получения липосом | |
| Lohumi | A novel drug delivery system: niosomes review | |
| CA2442539C (en) | Method and composition for solubilising a biologically active compound with low water solubility | |
| CA2818018C (en) | Liposomal formulation of dalcetrapib | |
| CN107427482A (zh) | 凝血酸的多囊脂质体制剂 | |
| AU2002312777A1 (en) | Method and composition for solubilising a biologically active compound with low water solubility | |
| AU763945B2 (en) | Oil-core compositions for the sustained release of hydrophobic drugs | |
| EP0514506B1 (en) | Lipid formulation system | |
| JP3245955B2 (ja) | リポソーム | |
| CA3018670A1 (en) | Viscoelastic gel of liraglutide adapted for once-weekly or once bi-weekly administration | |
| KR20180070667A (ko) | 주입액 또는 주사액으로서 및 주입용 농축액의 정맥내 투여를 위한 개선된 레보시멘단 제형 | |
| JP2009507006A (ja) | 鉄キレート剤を含む医薬組成物 | |
| Maheswaran et al. | Liposomal drug delivery systems—a review | |
| JP2021502337A (ja) | 関節内適用のための持続放出製剤 | |
| JP2653245B2 (ja) | 脂肪乳剤 | |
| US20040213837A1 (en) | Oil-core compositions for the sustained release of hydrophobic drugs | |
| JPH04356421A (ja) | プロスタグランジン類含有脂肪小体組成物 | |
| CN107375212B (zh) | 一种托匹司他脂质体制剂及其制备方法 | |
| CA3182955A1 (en) | Methods for preparing liposomal formulations | |
| Gregory | Preparation of Liposomes and Oily Formulations by Freeze-Drying of Monophase Solutions | |
| FR3119325A1 (fr) | Compositions liposomales orales | |
| Gregoriadis | Preparation of Liposomes and Oily Formulations by Freeze-Drying of Monophase Solutions.............. ChunLei Li, YingJie Deng, and JingXia Cui |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20130515 |
|
| MKLA | Lapsed |
Effective date: 20171205 |